HCID 86727498, compound → HCID 86727500, compound

HRID 519117Notes

Reaction equation

HRID 519117 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C@@H:13]([C:15]2[CH:16]=[C:17]3[C:26](=[CH:27][C:28]=2[C:29]([CH3:31])=[CH2:30])[O:25][CH2:24][C:23]2[N:18]3[C@H:19]([CH3:33])[C:20](=[O:32])[NH:21][N:22]=2)[CH3:14])([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C@@H:13]([C:15]2[CH:16]=[C:17]3[C:26](=[CH:27][C:28]=2[CH:29]([CH3:31])[CH3:30])[O:25][CH2:24][C:23]2[N:18]3[C@H:19]([CH3:33])[C:20](=[O:32])[NH:21][N:22]=2)[CH3:14])([CH3:12])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86727498HCID 86727498, compound

Product 1

HCID 86727500HCID 86727500, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-[(R)-1-((R)-7-isopropenyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-ethyl]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.0795 g, 0.175 mmol) and 10% Pd/C (0.037 g, 0.035 mmol) in MeOH (10 mL) was stirred under H2 for 1 h at rt. The reaction mixture was filtered, the filtrate was evaporated to dryness and the residue was purified by prep-TLC (eluting with 50% EtOAc in petroleum ether) to give 3-[(R)-1-((R)-7-isopropyl-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-ethyl]-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.061 g, 76%) as a solid. LC/MS (Table 1, Method 4) Rt=2.972 min.; MS m/z: 457 [M+H]+. 1H NMR (CDCl3, 400 MHz): δ 8.03 (brs, 1H), 7.00-6.92 (m, 1H), 6.64 (brs, 1H), 4.77-4.70 (m, 1H), 4.65-4.52 (m, 2H), 3.92-3.79 (m, 2H), 3.57-3.51 (m, 1H), 3.45 (m, 1H), 3.30 (m, 1H), 3.23-3.14 (m, 1H), 1.55-1.45 (m, 12H), 1.34-1.24 (m, 12H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. customthe residue was purified by prep-TLC (eluting with 50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-fcd0c8fad39e456b85f55bd8824b1475
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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